Leaders & Legacies

Alan Gregerman nearly lost everything after a stroke robbed him of his ability to speak and see. But instead of giving in, he turned that moment into one of his greatest leadership lessons. In this episode, Alan shares how navigating life without communication forced him to rethink how leaders engage, innovate, and lead. Through his recovery, he uncovered deeper truths about humility, clarity, and the need to constantly evolve.Alan breaks down why most organizations fail at innovation—and how the smartest people in the room may not be the answer. His latest book, The Wisdom of Ignorance, argues that not knowing is often the key to seeing clearly and moving boldly. He introduces his six-part framework for unlocking genius: be purposeful, curious, humble, respectful, future-focused, and yes—just a bit paranoid.With stories from his own life and business consulting career, Alan makes a compelling case for breaking with expertise, embracing fresh perspectives, and looking outside your industry for inspiration.Want to learn more about Alan Gregerman's work? Check out their website at https://www.alangregerman.com.Connect with Alan Gregerman on LinkedIn at https://www.linkedin.com/in/alan-gregerman-a33b236/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Emily Erstad joins Craig Andrews for a candid conversation about the real heart of leadership—emotional intelligence. A former speech-language pathologist turned hospice leader, Emily shares how leading in high-stakes environments taught her the power of trust, vulnerability, and consistency.She explains why leadership isn’t about commanding—it’s about partnering. Whether guiding patients through recovery or teams through chaos, Emily leans into emotional truth over cold logic. She emphasizes that great leaders don’t just give direction—they create safety, clarity, and alignment in moments of fear or uncertainty.Drawing from her book It’s Not That Deep, Emily discusses how her own struggles and leadership pivots helped her shape a human-centric approach to influence and impact. She also reveals how building teams that thrive without her has become her quiet legacy.Want to learn more about Emily Erstad’s work? Check out her website at https://eepublicationsllc.wixsite.com/ee-publications.Connect with Emily Erstad on LinkedIn at https://www.linkedin.com/in/emily-erstad-m-a-ccc-slp-381346135/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Lee Pepper brings battlefield-tested leadership into the boardroom. In this episode, Lee breaks down how military strategies—some dating back to the Romans—can drive success in today’s marketing and business landscape. Drawing from his Army background, time at Fort Knox, and career in behavioral healthcare marketing, Lee explains how setting clear intent and empowering teams to execute leads to superior outcomes.He makes the case for clarity over control and strategy over tactics. Citing leaders like Patton, Schwarzkopf, and Ross Perot, Lee calls out the real enemy: indecision. Whether in combat or campaign strategy, action wins. Leadership isn’t about managing from a spreadsheet—it’s about removing barriers and letting your people attack the mission.Lee also dives into how old-school intelligence gathering—listening to 10,000+ sales calls—has given him insights that most companies miss. His advice is simple and sharp: stop micromanaging, start trusting, and use history as your manual.Want to learn more about Lee Pepper's work? Check out their website at https://www.NeverOutmatchedBook.com.Connect with Lee Pepper on LinkedIn at https://www.linkedin.com/in/leepepper/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Stan Sukhinin knows what it’s like to rebuild from scratch. After a meteoric rise in Eastern Europe’s finance world—managing a $450M mezzanine loan portfolio—he moved to New York to launch a hedge fund. It didn’t survive the pandemic. What did survive? His ability to spot financial blind spots and fix them fast.Now, as founder of The Sorso, Stan serves as a fractional CFO for outpatient clinics across the U.S. He combines deep financial rigor with AI-powered forecasting to help healthcare providers operate with precision. In this episode, Stan breaks down the unique challenges in the outpatient clinic model—especially the widespread misreporting of revenue due to insurance reimbursement complexity.He shares why many seemingly healthy businesses collapse overnight, and how bad debt, shallow risk planning, and poor scenario modeling are usually to blame. For clinic owners and business leaders alike, Stan offers practical insight into financial structure, AI use cases, and creating stability in volatile times.Want to learn more about Stan Sukhinin's work? Check out their website at https://www.thesorso.com.Connect with Stan Sukhinin on LinkedIn at https://www.linkedin.com/in/stan-sukhinin/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Hark Herold brings three decades of military precision to the entrepreneurial world. As a retired U.S. Air Force colonel turned EOS implementer, Hark shares how his leadership experience in high-stakes environments—from serving in Desert Storm to overseeing base recovery during rocket attacks in Iraq—shaped his approach to business.Now, he empowers small and medium-sized businesses to build clarity, cohesion, and execution with the Entrepreneurial Operating System (EOS). In this episode, Hark explains why leadership alignment is non-negotiable, how ego can cripple growth, and what it means to have the “right people in the right seats.” He also highlights resources available for veteran-owned businesses and shares why coaching is essential, even when all the tools are already at your fingertips.Want to learn more about Hark Herold's work? Check out their website at https://www.eosworldwide.com/hark-herold.Connect with Hark Herold on LinkedIn at https://www.linkedin.com/in/joeharkherold/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Hillary Gale didn’t just pivot careers—she rewrote the script entirely. A former college writing teacher, she stepped away from academia, launched a one-woman marketing firm, and then discovered she was pregnant—all within days. With nine months on the clock, she had to lead fast, build smart, and carve out space for maternity leave while launching Moneta Copy.In this episode, Hillary breaks down how strong writing skills are foundational to leadership. She challenges the myth that good writing must follow rigid rules, arguing instead for authenticity, emotion, and real connection. Craig and Hillary dig into what makes content persuasive, how AI is changing the writing landscape, and why personal voice still matters.Her story is a lesson in resilience and resourcefulness. She didn’t wait for permission to lead—she made the deadline non-negotiable. If you’re a business owner relying on stale content and ChatGPT shortcuts, this conversation will remind you that powerful words—and clear leadership—still win.Want to learn more about Hillary Gale's work? Check out her website at https://monetacopy.com.Connect with Hillary Gale on LinkedIn at https://www.linkedin.com/in/hillary-meehan/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Donovan Ryckis is leading a healthcare revolution—one grounded in leadership, accountability, and total transparency. As CEO of Ethos Benefits, he exposes the broken incentives in traditional benefits brokerage, where rising premiums often pad broker commissions. His fiduciary approach flips the model: no backdoor deals, no hidden fees, and no vague renewals. Just clear numbers and bold decisions.In this episode, Donovan walks through how he saved a client from a 37% rate hike—without cutting coverage. He explains how ERISA laws make employers responsible for plan decisions, even if they don't understand them. He also breaks down how healthcare lawsuits are forcing CEOs, CFOs, and HR leaders to take their fiduciary duties seriously—or face legal consequences.Donovan doesn’t talk about leadership in theory—he practices it by telling hard truths, navigating complex data, and challenging a system rigged for opacity. This episode is a must-listen for any leader responsible for a company’s healthcare decisions.Want to learn more about Donovan Ryckis' work? Check out his website at https://www.EthosBenefits.com.Connect with Donovan Ryckis on LinkedIn at https://www.linkedin.com/in/donovanryckis.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Alex Sanfilippo shares how a childhood marked by dyslexia and self-doubt evolved into a leadership platform spanning podcasting, public speaking, and entrepreneurship. As the founder of PodMatch, Alex has enabled thousands of leaders to get their voices heard, but his path started with personal healing and self-expression.In this episode, Alex details how podcasting became his tool for leadership—helping him own his voice, refine his message, and grow his confidence. He makes the case for why CEOs and founders shouldn’t delegate guest appearances or hosting duties. Alex argues that being the voice of your company is irreplaceable when building connection and trust.He also explains why podcasting isn’t just a marketing tool—it’s an engine for clarity, learning, and growth. Whether it’s guesting to articulate your message or hosting to expand your network, Alex views podcasting as one of the most strategic moves a leader can make.Want to learn more about Alex Sanfilippo's work? Check out their website at https://podmatch.com/.Connect with Alex Sanfilippo on LinkedIn at https://www.linkedin.com/in/alexsanfilippo/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Chris Hurn, CEO of Community Bankshares, joined the show to talk straight about entrepreneurial leadership in high-stakes environments. He traces his roots to watching his single mother run a chocolate business out of their basement, an early masterclass in grit, marketing, and operations. That foundation shaped his view of what it means to lead—not just manage.Now a leader in small business financing, Chris outlines the crucial difference between being an entrepreneur and becoming a CEO. He explains how leaders must eventually move beyond scrappiness and take calculated risks with debt to scale their companies. But he’s quick to note that optimism must be balanced with pragmatism. Cash flow—not charisma—is what gets a loan approved.Chris also unpacks the coming wave of business acquisitions driven by baby boomer retirements, sharing insights on what industries are hot and where private equity is warping the landscape. His message is clear: real leadership is about seeing around corners and backing up vision with execution.Want to learn more about Chris Hurn’s work? Check out their website at https://www.phxbusiness.com.Connect with Chris Hurn on LinkedIn at https://www.linkedin.com/in/chrishurn/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Allison De Paoli joins Craig Andrews to break down how employers can lead through one of the most neglected aspects of their business—health insurance. Drawing from decades of experience and her family’s entrepreneurial legacy, Allison shows how leaders can stop hemorrhaging money on bloated health plans and start using benefits as a tool for retention, loyalty, and long-term cost control.She argues the system isn’t broken—it’s rigged. But with the right strategy, employers can bypass middlemen, reclaim fiduciary control, and offer high-quality care without budget blowouts. Allison walks through real-world examples of employers who’ve turned skyrocketing premiums into savings—without shifting the cost burden onto employees.If you lead a team and think better healthcare is out of reach, this episode will challenge that belief—and give you a roadmap to lead differently.Want to learn more about Allison De Paoli's work? Check out their website at https://www.altiqe.com.Connect with Allison De Paoli on LinkedIn at https://www.linkedin.com/in/allison-de-paoli/.Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.